fix(mobile): compact stale Claude threads before sending

apps/mobile/src/state/thread-outbox-model.ts

@@ -56,6 +56,7 @@ export const QueuedThreadMessageSchema = Schema.Struct({
   attachments: Schema.Array(DraftComposerAttachmentSchema),
   modelSelection: Schema.optional(ModelSelection),
   dispatchMode: Schema.optional(Schema.Literals(["auto", "queue", "steer", "restart"])),
+  compactBeforeSend: Schema.optional(Schema.Boolean),
   runtimeMode: Schema.optional(RuntimeMode),
   interactionMode: Schema.optional(ProviderInteractionMode),
   creation: Schema.optional(QueuedThreadCreationSchema),
@@ -89,6 +90,8 @@ export interface QueuedThreadMessage {
   readonly interactionMode?: ProviderInteractionModeType;
   /** Captured at enqueue because draining may occur long after the tap. */
   readonly dispatchMode?: ComposerDispatchMode;
+  /** Sends "When you return"'s `/compact` ahead of the message, which queues behind it. */
+  readonly compactBeforeSend?: boolean;
   readonly creation?: QueuedThreadCreation;
   readonly createdAt: string;
 }

apps/mobile/src/state/thread-outbox.test.ts

@@ -329,6 +329,8 @@ describe("thread outbox", () => {
       },
       runtimeMode: "approval-required",
       interactionMode: "plan",
+      dispatchMode: "queue",
+      compactBeforeSend: true,
     } satisfies QueuedThreadMessage;
 
     expect(decodeQueuedThreadMessage(encodeQueuedThreadMessage(selectedMessage))).toEqual(

apps/mobile/src/state/thread-task-permissions.test.ts

@@ -333,6 +333,7 @@ describe("mobile handoff preview and submission", () => {
       auth: { status: "authenticated" as const },
       availability: "available" as "available" | "unavailable",
       models: [{ slug: selection.model }],
+      slashCommands: [],
     };
     const projectOverride = { enabled: false };
     state.serverConfig = {

apps/mobile/src/state/threadOutboxDelivery.permissions.test.ts

@@ -498,3 +498,52 @@ describe("queued task operation access", () => {
     },
   );
 });
+
+describe("compaction before a queued send", () => {
+  const compactTurn = {
+    commandId: "command:compact",
+    message: {
+      messageId: "message:compact",
+      role: "user",
+      text: "/compact",
+      attachments: [],
+      idleCompaction: "onReturn",
+    },
+    dispatchMode: "queue",
+  };
+
+  it("queues /compact ahead of the message and resends the same /compact on a retry", async () => {
+    setOperateGrant("secondary", true);
+    const queued = message({ compactBeforeSend: true, dispatchMode: "queue" });
+    await state.manager.enqueue(queued);
+    state.start
+      .mockResolvedValueOnce(AsyncResult.success({}))
+      .mockResolvedValueOnce(AsyncResult.failure(Cause.fail(new Error("Socket is not connected"))));
+    await runDrain();
+    expect(remaining()).toEqual([queued]);
+
+    // A restarted app delivers the persisted message again.
+    state.cleanups.splice(0).forEach((cleanup) => cleanup());
+    await runDrain();
+    expect(state.start.mock.calls.map(([call]) => call.input)).toEqual([
+      expect.objectContaining(compactTurn),
+      expect.objectContaining({ commandId: "command", dispatchMode: "queue" }),
+      expect.objectContaining(compactTurn),
+      expect.objectContaining({ commandId: "command", dispatchMode: "queue" }),
+    ]);
+    expect(remaining()).toEqual([]);
+  });
+
+  it("holds the message when its /compact cannot be sent", async () => {
+    setOperateGrant("secondary", true);
+    const queued = message({ compactBeforeSend: true, dispatchMode: "queue" });
+    await state.manager.enqueue(queued);
+    state.start.mockResolvedValueOnce(
+      AsyncResult.failure(Cause.fail(new Error("Socket is not connected"))),
+    );
+    await runDrain();
+    expect(state.start).toHaveBeenCalledOnce();
+    expect(state.start.mock.calls[0]?.[0].input).toMatchObject(compactTurn);
+    expect(remaining()).toEqual([queued]);
+  });
+});

apps/mobile/src/state/threadOutboxDelivery.ts

@@ -16,9 +16,9 @@ import {
   CommandId,
   DEFAULT_PROVIDER_INTERACTION_MODE,
   DEFAULT_RUNTIME_MODE,
+  MessageId,
   PROVIDER_SEND_TURN_MAX_ATTACHMENTS,
   type EnvironmentId,
-  type MessageId,
 } from "@t3tools/contracts";
 import { buildTemporaryWorktreeBranchName } from "@t3tools/shared/git";
 import * as Cause from "effect/Cause";
@@ -864,6 +864,37 @@ export function createThreadOutboxDelivery(): {
       settings,
       currentConfig.providers,
     );
+    if (queuedMessage.compactBeforeSend === true) {
+      if (!hasAccess()) return true;
+      // Queued, since steering a running turn with a compaction is rejected.
+      const compactionResult = await runDeliveryCommand(threadEnvironment.startTurn, {
+        environmentId: queuedMessage.environmentId,
+        input: {
+          commandId: settingsCommandId(queuedMessage, "compact"),
+          creationSource: "mobile",
+          threadId: queuedMessage.threadId,
+          message: {
+            messageId: MessageId.make(`${queuedMessage.messageId}:compact`),
+            role: "user",
+            text: "/compact",
+            attachments: [],
+            idleCompaction: "onReturn",
+          },
+          modelSelection: sendSettings.modelSelection,
+          runtimeMode: sendSettings.runtimeMode,
+          interactionMode: sendSettings.interactionMode,
+          createdAt: queuedMessage.createdAt,
+          dispatchMode: "queue",
+        },
+      });
+      if (AsyncResult.isFailure(compactionResult) && !hasAccess()) return true;
+      const compactionFailure = reportCommandFailure(queuedMessage, compactionResult, "start-turn");
+      if (compactionFailure?.action === "retry") return false;
+      if (compactionFailure?.action === "restore") {
+        return restoreQueuedMessage(persistedMessage, compactionFailure.message);
+      }
+      if (!isQueuedMessagePayloadCurrent(persistedMessage, deliveryRevision)) return true;
+    }
     if (!hasAccess()) return true;
     const deliveryResult = await runDeliveryCommand(threadEnvironment.startTurn, {
       environmentId: queuedMessage.environmentId,

apps/mobile/src/state/use-thread-composer-state.ts

@@ -3,6 +3,7 @@ import * as Dialog from "../components/ui/Dialog";
 import { AuthOrchestrationOperateScope } from "@t3tools/contracts";
 import { readEnvironmentScope } from "./session";
 import { useAtomValue } from "@effect/atom-react";
+import { shouldCompactBeforeSend } from "@t3tools/client-runtime/state/context-window";
 import { threadRuntimeIsActive } from "@t3tools/client-runtime/state/shell";
 import type { ThreadCheckpointSummary } from "@t3tools/client-runtime/state/thread-checkpoints";
 import { resolvePendingHandoff } from "@t3tools/client-runtime/handoff";
@@ -656,6 +657,25 @@ export function useThreadComposerState() {
           : "auto";
 
     const metadata = makeQueuedMessageMetadata();
+    const compactBeforeSend =
+      followUpDispatchMode === null &&
+      selectedEnvironmentRuntime?.connectionState === "connected" &&
+      selectedThreadProjection !== null &&
+      serverConfig != null &&
+      shouldCompactBeforeSend({
+        projection: selectedThreadProjection.projection,
+        visibleTurnItems: selectedThreadVisibleTurnItems,
+        selection: modelSelection,
+        providers: serverConfig.providers,
+        settings: serverConfig.settings,
+        text,
+        threadIdle:
+          !activeThreadBusy &&
+          !runlessWorkActive &&
+          !isCompacting &&
+          selectedThreadQueuedMessages.length === 0,
+        now: metadata.createdAt,
+      });
     const messageId = MessageId.make(metadata.messageId);
     clearThreadComposerError(threadKey);
     const enqueuePromise = enqueueThreadOutboxMessage({
@@ -672,7 +692,11 @@ export function useThreadComposerState() {
         provider,
         draft.interactionMode ?? thread.interactionMode,
       ),
-      ...(followUpDispatchMode === null ? {} : { dispatchMode: followUpDispatchMode }),
+      ...(compactBeforeSend
+        ? { compactBeforeSend, dispatchMode: "queue" as const }
+        : followUpDispatchMode === null
+          ? {}
+          : { dispatchMode: followUpDispatchMode }),
       createdAt: metadata.createdAt,
     });
     clearComposerDraftContent(threadKey, { deferAttachmentCleanup: true });

apps/web/src/components/ChatView.logic.ts

@@ -4,6 +4,7 @@ import {
   deriveThreadRuntime,
 } from "@t3tools/client-runtime/state/thread-execution";
 import { checkpointFileTotals } from "@t3tools/client-runtime/state/thread-checkpoints";
+import { COMPACT_COMMAND_PATTERN } from "@t3tools/client-runtime/state/context-window";
 import { derivePendingBackgroundWork } from "@t3tools/shared/orchestrationV2PendingBackgroundWork";
 import {
   latestUnheldRun,
@@ -833,10 +834,6 @@ export function shouldShowPlanFollowUpPrompt(input: {
   );
 }
 
-// A typed `/compact`, with or without instructions, is already the compaction. Queueing a
-// bare one ahead of it would run an uninstructed compaction first and charge for two.
-const COMPACT_COMMAND_PATTERN = /^\/compact(?:\s|$)/i;
-
 const sessionDismissedBranchMismatchKeys = new Set<string>();
 
 export function dismissBranchMismatchForSession(key: string): void {

apps/web/src/components/ChatView.tsx

@@ -310,15 +310,13 @@ import { ComposerBannerStack, type ComposerBannerStackItem } from "./chat/Compos
 import { modelFallbackBannerItem } from "./chat/ComposerUsageLimits";
 import { ComposerSurface } from "./chat/ComposerSurface";
 import { resolveThreadSyncPhase } from "../threadSync";
-import {
-  hasAvailableCompactionProvider,
-  hasDismissedResumeCompaction,
-  shouldOfferResumeCompaction,
-} from "./chat/ContextWindowMeter.logic";
+import { hasAvailableCompactionProvider } from "./chat/ContextWindowMeter.logic";
 import {
   deriveLatestContextWindowSnapshot,
+  hasDismissedResumeCompaction,
   latestProviderTurnTokenUsage,
-} from "../lib/contextWindow";
+  shouldOfferResumeCompaction,
+} from "@t3tools/client-runtime/state/context-window";
 import {
   MOBILE_COMPOSER_VIEW_TRANSITION_NAME,
   MOBILE_DRAFT_HEADLINE_VIEW_TRANSITION_NAME,

apps/web/src/components/chat/ChatComposer.tsx

@@ -250,7 +250,7 @@ import {
   resolveComposerDispatchMode,
   type ComposerDispatchMode,
 } from "@t3tools/client-runtime/state/composer-dispatch";
-import type { ContextWindowSnapshot } from "../../lib/contextWindow";
+import type { ContextWindowSnapshot } from "@t3tools/client-runtime/state/context-window";
 import {
   resolveProviderSkillsForCwd,
   resolveProviderSlashCommandsForCwd,

apps/web/src/components/chat/ComposerFooterControls.tsx

@@ -8,7 +8,7 @@ import { createModelSelection } from "@t3tools/shared/model";
 import { BotIcon, PencilRulerIcon } from "lucide-react";
 import { type ComponentProps, memo, useId, useRef, useState } from "react";
 
-import type { ContextWindowSnapshot } from "../../lib/contextWindow";
+import type { ContextWindowSnapshot } from "@t3tools/client-runtime/state/context-window";
 import { Menu as MenuPrimitive } from "@base-ui/react/menu";
 import { Menu, MenuPopup, MenuTrigger } from "../ui/menu";
 import { Tooltip, TooltipPopup, TooltipTrigger } from "../ui/tooltip";

apps/web/src/components/chat/ContextWindowMeter.logic.test.ts

@@ -1,9 +1,9 @@
 import { ProviderDriverKind, ProviderInstanceId, type ServerProvider } from "@t3tools/contracts";
 import { describe, expect, it } from "vite-plus/test";
 import { deriveProviderInstanceEntries } from "../../providerInstances";
+import { hasDismissedResumeCompaction } from "@t3tools/client-runtime/state/context-window";
 import {
   hasAvailableCompactionProvider,
-  hasDismissedResumeCompaction,
   resolveContextWindowModelDisplayName,
   shouldReserveContextWindowMeter,
 } from "./ContextWindowMeter.logic";

apps/web/src/components/chat/ContextWindowMeter.logic.ts

@@ -1,18 +1,10 @@
 import type { ModelSelection, ProviderDriverKind, ProviderInstanceId } from "@t3tools/contracts";
-import {
-  CLAUDE_RESUME_COMPACTION_NEVER_ANSWER,
-  COMPACTION_SUGGESTION_MIN_TOKENS,
-  isClaudeResumeCompactionQuestion,
-} from "@t3tools/shared/claudeCompaction";
 import {
   resolveSelectableProviderInstanceEntry,
   type ProviderInstanceEntry,
 } from "../../providerInstances";
 import { getDisplayModelName, type ModelEsque } from "./providerIconUtils";
 
-// Fallback TTL: Claude's 1h cache plus slack.
-const CLAUDE_RESUME_COMPACTION_FALLBACK_MS = 70 * 60_000;
-
 export function providerSupportsManualCompaction(
   provider: ProviderInstanceEntry | null | undefined,
 ): boolean {
@@ -43,47 +35,6 @@ export function hasAvailableCompactionProvider(input: {
   );
 }
 
-export function hasDismissedResumeCompaction(
-  activities: ReadonlyArray<{ readonly kind: string; readonly payload: unknown }>,
-): boolean {
-  return activities.some((activity) => {
-    if (activity.kind !== "user-input.resolved") return false;
-    const payload = activity.payload;
-    if (!payload || typeof payload !== "object") return false;
-    const answers = (payload as { readonly answers?: unknown }).answers;
-    if (!answers || typeof answers !== "object" || Array.isArray(answers)) return false;
-
-    return Object.entries(answers).some(
-      ([question, answer]) =>
-        isClaudeResumeCompactionQuestion(question) &&
-        answer === CLAUDE_RESUME_COMPACTION_NEVER_ANSWER,
-    );
-  });
-}
-
-export function shouldOfferResumeCompaction(input: {
-  readonly provider: string | null | undefined;
-  readonly usedTokens: number | null | undefined;
-  readonly updatedAt: string | null | undefined;
-  readonly promptCacheTtlMs?: number | undefined;
-  readonly now: string;
-}): boolean {
-  if (
-    input.provider !== "claudeAgent" ||
-    (input.usedTokens ?? 0) < COMPACTION_SUGGESTION_MIN_TOKENS
-  ) {
-    return false;
-  }
-
-  const updatedAt = Date.parse(input.updatedAt ?? "");
-  const now = Date.parse(input.now);
-  return (
-    Number.isFinite(updatedAt) &&
-    Number.isFinite(now) &&
-    now - updatedAt >= (input.promptCacheTtlMs ?? CLAUDE_RESUME_COMPACTION_FALLBACK_MS)
-  );
-}
-
 export function resolveContextWindowModelDisplayName(
   selection: ModelSelection | null | undefined,
   modelOptionsByInstance: ReadonlyMap<ProviderInstanceId, ReadonlyArray<ModelEsque>>,

apps/web/src/components/chat/ContextWindowMeter.tsx

@@ -1,5 +1,6 @@
 import { Button } from "../ui/button";
-import { type ContextWindowSnapshot, formatContextWindowTokens } from "~/lib/contextWindow";
+import type { ContextWindowSnapshot } from "@t3tools/client-runtime/state/context-window";
+import { formatContextWindowTokens } from "~/lib/contextWindow";
 import { Popover, PopoverPopup, PopoverTrigger } from "../ui/popover";
 import {
   formatContextWindowCompactionMessage,

apps/web/src/components/chat/ThreadDetailsUsage.tsx

@@ -16,7 +16,8 @@ import type { ReactNode } from "react";
 
 import { usePrimarySettings } from "../../hooks/useSettings";
 import { useNowMinute } from "../../hooks/useNowMinute";
-import { type ContextWindowSnapshot, formatContextWindowTokens } from "../../lib/contextWindow";
+import type { ContextWindowSnapshot } from "@t3tools/client-runtime/state/context-window";
+import { formatContextWindowTokens } from "../../lib/contextWindow";
 import { cn } from "../../lib/utils";
 import { formatUpcomingTimestamp } from "../../timestampFormat";
 import { Tooltip, TooltipPopup, TooltipTrigger } from "../ui/tooltip";

apps/web/src/lib/contextWindow.test.ts

@@ -11,8 +11,11 @@ import {
   ThreadId,
 } from "@t3tools/contracts";
 import { makeThreadProjectionFixture } from "../test-fixtures";
-import { shouldOfferResumeCompaction } from "../components/chat/ContextWindowMeter.logic";
-import { deriveLatestContextWindowSnapshot, latestProviderTurnTokenUsage } from "./contextWindow";
+import {
+  deriveLatestContextWindowSnapshot,
+  latestProviderTurnTokenUsage,
+  shouldOfferResumeCompaction,
+} from "@t3tools/client-runtime/state/context-window";
 
 const decodeTokenUsage = Schema.decodeSync(OrchestrationV2ProviderTurnTokenUsage);